Datadog CFO plans $2.3M Rule 144 stock sale

Datadog CFO David Obstler filed a Rule 144 notice covering 10,000 Class A shares, with prior 10b5-1 sales also disclosed.

Rhea-AI Filing Summary

Datadog, Inc. (DDOG) received a notice that its Chief Financial Officer, David Obstler, plans to sell 10,000 shares of Class A common stock through Morgan Stanley Smith Barney. The notice cites 334,904,614 shares of Class A common stock outstanding as of September 21, 2026. The shares to be sold were acquired via vesting of restricted stock units between June 1, 2022 and September 1, 2023 and performance stock units on September 1, 2023, all previously registered on Form S‑8. The filing also lists recent Rule 10b5‑1 sales by Obstler and related trusts over the past three months.

Key Figures

Shares to be sold under Rule 144: 10,000 shares Aggregate market value of planned sale: $2,299,200.00 Class A shares outstanding: 334,904,614 shares +5 more

8 metrics

Shares to be sold under Rule 144 10,000 shares Planned sale of Datadog Class A common stock by CFO David Obstler

Aggregate market value of planned sale $2,299,200.00 Value reported for the 10,000 Class A shares covered by the notice

Class A shares outstanding 334,904,614 shares Class A common stock outstanding as of September 21, 2026; baseline figure

RSU shares to be sold 8,479 shares Class A shares acquired from restricted stock units vested on June 1, 2022

PSU shares to be sold 1,521 shares Class A shares acquired from performance stock units vested on September 1, 2023

Recent 10b5-1 sale by CFO 40,000 shares for $9,098,879.00 Class A shares sold on September 14, 2026 by David Obstler

Recent 10b5-1 sale by each children’s trust 12,000 shares for $2,729,663.70 Class A shares sold on September 14, 2026 by each 2019 children’s trust

Additional recent sale by CFO 16,524 shares for $3,518,027.35 Class A shares sold on September 2, 2026 by David Obstler

Key Terms

Rule 144, Restricted Stock Units, Performance Stock Units, Form S-8, +1 more

5 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144"

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Restricted Stock Units financial

"The securities to be sold were acquired upon the vesting of restricted stock units"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

Performance Stock Units financial

"and performance stock units on 09/01/2023"

Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.

Form S-8 regulatory

"were registered on Form S-8"

A Form S-8 is a U.S. Securities and Exchange Commission registration that lets a public company set aside shares for employee benefit plans and stock-based compensation. Think of it as opening a dedicated account that authorizes the company to issue or reserve stock for workers and directors; it matters to investors because it enables share dilution when those awards are granted or exercised and signals how management is compensated and incentivized.

10b5-1 regulatory

"10b5-1 Sales for DAVID OBSTLER"

A 10b5-1 plan is a pre-set schedule that lets company insiders buy or sell shares according to written instructions made when they do not possess material, nonpublic information. Think of it as a timed automatic payment for stock trades: it helps insiders avoid accusations of trading on secret information and gives outside investors a clearer signal about whether sales are routine or potentially informative about the company’s prospects.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does the Form 144 filing disclose for Datadog (DDOG)?

It discloses that CFO David Obstler filed a notice to sell 10,000 shares of Datadog Class A common stock under Rule 144, with the shares acquired from vested restricted stock units and performance stock units previously registered on Form S-8.

How many Datadog (DDOG) shares are covered by the planned Rule 144 sale?

The notice covers a planned sale of 10,000 shares of Datadog Class A common stock. These shares are to be sold through Morgan Stanley Smith Barney LLC Executive Financial Services according to the Rule 144 filing.

What was the aggregate market value of the Datadog (DDOG) shares in the Form 144?

The Form 144 lists an aggregate market value of $2,299,200.00 for the 10,000 Class A common shares covered by the notice, based on the pricing information included in the filing’s securities information section.

How many Datadog (DDOG) shares were outstanding as referenced in the filing?

The filing cites 334,904,614 shares of Datadog Class A common stock outstanding as of September 21, 2026; this is provided as context for the Rule 144 notice and is not the amount being sold.

What prior 10b5-1 sales by David Obstler are disclosed for Datadog (DDOG)?

The filing lists 40,000 shares sold on September 14, 2026 for $9,098,879.00 by David Obstler, plus 16,524 shares sold on September 2, 2026 for $3,518,027.35, in addition to sales by related 2019 children’s trusts.

What recent trust sales related to Datadog (DDOG) are mentioned?

Two 2019 children’s trusts for Alison and Andrew Obstler each sold 12,000 Datadog Class A shares on September 14, 2026, with each transaction totaling $2,729,663.70, as part of 10b5-1 sales disclosed in the Rule 144 filing.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/21/2026 - 04:35 PM Accepted by SEC EDGAR 09/21/2026 - 04:35 PM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001120741
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	Datadog, Inc.
SEC File Number	001-39051
Address of Issuer	620 8th Avenue, 45th Floor New York NEW YORK 10018
Phone	8663294466
Name of Person for Whose Account the Securities are To Be Sold	DAVID OBSTLER
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Class A Common	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	10000	2299200.00	334904614	09/21/2026	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Class A Common	06/01/2022	Restricted Stock Units	Issuer			8479	06/01/2022	N/A
Class A Common	09/01/2023	Performance Stock Units	Issuer			1521	09/01/2023	N/A

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
10b5-1 Sales for DAVID OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/14/2026	40000	9098879.00
10b5-1 Sales for DAVID OBSTLER CHILDREN 2019 TRUST FBO ALISON OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/14/2026	12000	2729663.70
10b5-1 Sales for DAVID OBSTLER CHILDREN 2019 TRUST FBO ANDREW OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/14/2026	12000	2729663.70
DAVID OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/02/2026	16524	3518027.35

144: Remarks and Signature

Remarks	The securities to be sold were acquired upon the vesting of restricted stock units during the period of 06/01/2022 through 09/01/2023 and performance stock units on 09/01/2023. Securities to be sold, acquired through RSU/PSU or upon option exercise, were registered on Form S-8
Date of Notice	09/21/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	06/13/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ David Obstler
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)